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His First Blowjob

"A shy student gets paired with his crush"

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Paul leaned back on his chair, looking at the dual monitor display in front of him and ensuring that the correct files were opened for the project. He still couldn't believe it, he had been paired with his high school crush, none other than the cheerleading captain, Annie.

He wasn't sure she even knew of his existence prior to the project designation, but it was the opposite for him, he knew all about her from the countless hours he had spent stalking her anonymously on social media. He knew her favorite artists, TV shows, sports teams, and clothing brands, but most importantly he knew the shape and size of her butt from all the times he had zoomed in on her pictures and replayed her videos.

He pressed his erection down to the side, hoping that it would be enough to hide it along with the tight boxers he was wearing. Normally, as a seventeen-year-old with raging hormones, he would tend to his needs with a visual aid compromised of a mixture of Annie's pictures and a carefully selected adult video of a similar-looking porn star, but he was too anxious for that as he waited for her to arrive at his home.

I hope she's wearing leggings, his pervy side intruded, letting his fantasies run wild. Or maybe even a skirt.

Just when he had managed to cool himself down, he heard the doorbell ring, which startled him back into a nervous state. He hurried out of his room only to realize that he didn't want to answer the door right away as to not seem overly excited, so he took a deep breath and slowed down on the way downstairs.

He greeted her at the door, keeping it simple to not mess up right out of the gate, but unable to stop his face from getting warmer as he stole a glance at her outfit that consisted of a blue, relaxed-fit shirt and formfitting, green shorts that appeared to be a size too small for her.

"My room's upstairs," he said, awkwardly pointing in the direction of it and moving out of the way to get two bottles of water he had preemptively placed next to the living room TV.

It was a shrewd move that invited her up the stairs before him so that he could follow her and get his first real-life close-up of her coveted backside.

Much better than leggings, those are basically panties, he thought, admiring how the shiny fabric of the shorts barely reached her thighs and outlined the shape of her butt.

After having done the best he could to contain his erection, it managed to free itself and tent his shorts in a matter of seconds, before he even got to the second floor.

In a last effort to save himself further embarrassment, he walked ahead of her into his room where he quickly sought refuge by sitting down and hoping the desk provided him with sufficient cover.

Once they began looking over the project tasks, he felt like a fish back in water, but he could still feel the warmness on his face and his aching member pushing against its constraints.

When he thought he was in the clear, she made a comment that brought him out of his short-lived comfort zone when she said, "You're blushing pretty hard."

"I, uh, I am?" he asked, feigning ignorance while the cold beads of sweat running down his forehead betrayed him.

"It's okay, I tend to have that effect on boys," she said, in such a nonchalant way that made his heart skip and his cock twitch.

He continued working, piecing the project together and adding her input where necessary, but unable to maintain his usual typing proficiency which she took notice of.

"Am I distracting you?" she asked, displaying a sexy innocence that he wasn't used to.

He shook his head, "No, erm, it's not that," he lied.

"Well, your dick has been hard this whole time," she added, in the same tone she had been using for details on the project.

"No, what, sorry," he said, caught off guard by the fact she had noticed all along.

"Look, I need a good grade or I'll be suspended from the squad," she explained, inching closer towards him.

"Yeah, of course, I got this," he said, reassuring her that she wouldn't receive an academic suspension.

"Make sure we get an A on the project," she said, in her soft and usually convincing voice, while reaching to place her hand dangerously close to his bulge.

"What, a-are you doing?" he asked, feeling his cock reacting to her caressing hand.

"Let me help you, you're not gonna be able to concentrate," she said, flashing her irresistible smile.

He knew her jump in logic was strange and that he didn't want to take advantage of her, but he wasn't about to interrupt his crush's inspiration in what was a once-in-a-lifetime opportunity. He rolled his chair back a bit, giving her enough space to get on her knees in front of him.

"Ever gotten one before?" she asked, as she hooked her fingers under the waistband of his shorts and boxers.

"No, never," he replied, knowing that he had yet to kiss or romantically touch the opposite sex.

"You have a nice dick though," she said as she unveiled his throbbing member and took a moment to inspect the reddish-purple color of his engorged head and his veiny shaft.

"Wait, er, I do?" he asked, caught between feeling flattered and surprised by her comment.

He was several pounds overweight, a virgin and an introvert who avoided overwhelming social activity while she was the opposite, with the physique required to be the cheerleading captain and the personality of a social butterfly who had dated multiple football players. Everything considered, hearing his crush compliment his size was a boost to his ego that he was not going to forget anytime soon.

She answered by looking up at him with her light blue eyes then sticking her tongue out and inching it closer to the underside of his cock. His throbbing shaft pulsed before her, showing its anticipation by oozing a drop of precum that she caught with her tongue as it trailed down near the base.

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In one long lick, she spread a thin coating of saliva all the way up his length until she reached the sensitive backside of his glans. She worked her tongue side to side on the erogenous spot then planted a kiss on it that challenged his orgasm control right out of the gate.

Her right hand wrapped around his girth, contrasting the softness of her palm against his rigidness, with her index finger and thumb barely able to connect around it. She gently squeezed it, making it throb even harder, before sealing her lips just past the tip.

No fucking way this is happening, he thought, looking down at his greatest fantasy playing out before his eyes.

Her glossy, pink lips worked halfway down his shaft, barely touching the top of her stroking hand and providing a rhythm of suction along with her caving cheeks. Light moans and gurgling sounds had replaced the sound of the keystrokes, but they were just as fundamental to the success of their project. His morale and confidence were increased while the stress of school dissipated rapidly between her sealed lips.

Her technique wasn't like the one he was used to seeing in the porn videos, it was more loving and tender, with her high, delicate cheekbones and eyes mesmerizing him. He placed his hand on the back of her head, caressing her strawberry blond hair, inadvertently urging her to up her intensity as she closed her eyes and cupped his scrotum with her free hand.

"You're beautiful, Annie," he said, realizing his thoughts had escaped out his mouth.

She moaned in response but didn't stop pleasuring him for a second. Instead, she jerked him with more vigor. The faster, harder strokes made him push his hips upwards, hinting to her that he was approaching his climax. She had been in this position many times as she was more experienced than her peers, and working her mouth for a creamy reward never failed to encourage her.

All his life he had thought the adage of opposites attract was utter nonsense, but he could no longer dismiss it, not when the popular cheerleader was on her knees servicing him. They were truly opposites in the societal spectrum but opportunity had intertwined their paths and the thought of a future with her was enough to send him over the edge.

"I'm g-gonna...come," he warned, a second too late as his first shot hit the roof of her mouth.

She broke the second shot with her tongue, swirling his warmth around his head, before opening her mouth and letting it trail down his shaft. She placed her hands on his thighs and welcomed him back into her mouth, this time taking him deeper until her lips touched the base of his shaft. The remaining shots of his load splashed against the back of her throat, putting an exclamation point on her completed objective and making his toes curl with the overwhelming post-orgasm sensation.

He would have liked more time to enjoy her, but reality set in quickly and urged them to retreat back to normality.

"Ohhmm, fuck, I didn't think you were gonna swallow," he said, attentively watching her wipe her mouth with her forearm.

"Of course, you have a good taste," she said, pushing off his thighs to get up on her feet.

He quickly pulled up his shorts and boxers to hide his softening member while she adjusted her bottoms that had slightly wedged on the backside.

"I, er, can help you study any time, you know, later when finals come up," he said, back in his usual shy demeanor.

"Um, yeah, maybe I'll take you up on that, thanks," she said, returning a gentle smile. "But I gotta get going now."

"Oh, uh, sure, no worries," he said, panicking in the back of his mind and hoping she didn't regret it. "I'll finish the rest of the project."

He accompanied her downstairs to the front door where they briefly talked about the final details for the project and exchanged numbers.

On the surface, he was the same person, struggling to find words and remaining red-faced, but something inside of him had changed. For the first time in his life, he took a leap of faith and swiftly reached behind her back to grab handfuls of her ass cheeks. To his relief, she smiled at his boldness, giving him the green light to squeeze her sculpted flesh. He had simulated doing so many times during his masturbatory sessions, fantasizing about their firmness, but to his surprise they were softer under his fingertips than he could have ever imagined.

"I'll text you," she said, cutting his inspiration short but making up for it by getting on her tiptoes to peck him on the cheek.

He held her close to him for a couple more seconds, wishing he could freeze time and remain in the moment indefinitely, before reluctantly letting her go and opening the door for her.

"See ya, Paul," she said.

"See you... later," he trailed off, unsure if she'd even heard but entranced by the sway of her hips all the way to her car.

Did she just say my name, he asked himself, smiling at what was a more innocent triumph for him than what had transpired in his room.

He had always felt that nothing went his way, that certain things were not for someone like him, but on this day such negativity had been dispelled, and the possibility of losing his virginity to his crush no longer seemed farfetched. For now, he would enjoy his victory, but soon he would start preparing for the final exams, with a special focus on the cheerleading captain's bubble butt.

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Written by Issabela
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